


Bet On

by Ookamisan



Series: Sexathoning [2]
Category: Teen Wolf (TV)
Genre: Alpha Derek, Anal Fingering, Anal Sex, Bad Dragon, Bottom Derek, Coming Untouched, Crying During Sex, Dildos, Fleshlights, Knotting, Knotting Dildos, M/M, Overstimulation, Sex Toys, Top Derek, competetive, powerbottom derek
Language: English
Status: Completed
Published: 2016-08-20
Updated: 2016-08-20
Packaged: 2018-08-09 23:49:40
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,760
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7822015
Author URL: https://archiveofourown.org/users/Ookamisan/pseuds/Ookamisan
Summary: <blockquote class="userstuff">
              <p>Stiles introduce another wacky sex act to challenge Derek</p>
            </blockquote>





	Bet On

**Author's Note:**

> Im suffering some major writers block with my other story. wrote this to try and get the brain juices going  
> heed tags  
> unbeta'd
> 
> Werewolf muzzle fleshlight: https://bad-dragon.com/images/product_images/product_photo_31_resized.jpg

"What in the world?" Derek excalimed, staring at the massively long dildo Stiles was wielding with a particularly worrisome glint in his eye.

"What... is _that_?" Derek pointed at it as if it was making crude faces at him. "You are not sticking that up my ass."

"Of course not!" Stiles said a little too exuberantly, bouncing on his heels. "I am going to put up _both_ our asses!" Stiles held it up a little higher.

Derek lost his breath at the knowledge that this sword length dildo was double ended. There were also a mass of smooth bumps encircling each end near the tips, and was complete with two small, but no less intimidating, knots.

"No."

Stiles pouted.

"Fine. What about this?" Stiles turns and grabs something off the bed and holds it up.

"What is that, a fleshlight?"

"Look closer." Stiles places it in Derek's broad palm.

He studies it and realizes it is indeed a type of fleshlight made of silicone. Solid black and, to his shock, designed to look like a wolf's muzzle howling. He raised an eyebrow to Stiles. "This is just offensive, Stiles."

"Oh and the knots arent?" Stiles rolls his eyes, waves away Derek's comment. "Come on are you really surprised anymore?"

"I shouldn't be. It's not that I'm surprised that you would come up with something like this. It's that there are actually people that are likeminded and make these available to you." Derek waved the wolf maw at him.

"My kinks are always with you in mind, Derek." Stiles winks at him, making him blush.

"Tomorrow, Stiles."

"Yes!"

\---

The next day Derek came home and immediately took a shower to freshen up and prepare himself to the night. He hated having to clean himself out. It took a long time and the noises were embarrassing as well as the feeling but when he was finally confident that he was clean, he knew it would be worth it.

He stepped out of the shower and into the bedroom. He finished toweling himself dry and opened up Stiles's ever growing drawer of sex toys, and grabbed a sizable plug and lube. The plug was between the size of a golf ball and a tennis ball. About the size and shape of a plastic easter egg toy. It was even bright green.

He spread the towel on the bedroom carpet and lay on his back. He had been practicing alone to surprise Stiles. He squirt a bit of lube on his finger tips and spread it along his hole, taking deep breaths and trying to release his anticipation. He massaged for a few minutes, making the outside loose and relaxed. When he pressed his middle finger in, it sunk with zero resistance. He curled and prodded, reminding himself what this felt like. It was a little embarrassing if he thought about it too much. When two fingers got no resistance he grabbed the plug and squirt a bit of lube on it, spreading it around.

He pressed it to himself and with a long exhale, slowly pushed it inside. His mouth opened with a little "ohh" as it stretched him and he felt his lower back and belly burn slightly with arousal. When the plug reached past the widest part, it suddenly popped in and he gasped and flinched. The base of the plug had a ring for your finger to hook into and when he felt it press against his perineum, his moaned softly.

He let himself lay there for a minute, refusing to touch his slowly hardening cock and just enjoy the fullness and pressure on his prostate. When his heart rate returned to normal, he slowly stood up and threw the towel into the hamper, and returned the lube to it's proper place.

He was sitting on the bed in a pair of old, loose pajama pants reading a book to occupy his time when Stiles got home.

"I'm home! I'm late but I'm home!" Derek heard Stiles drop his keys and backpack and make a mad dash to their bedroom and to the bathroom, slamming the door.

Derek stifled his laughter and turned the page in his book as Stiles audibly took his clothes off and got into the shower.

Derek listened to Stiles heart rate slow and his breathing even as the hot water calmed him.

By the time Stiles was done, Derek's anticipation had caught up with him as he slowly hardened in his night pants.

Stiles opened the bathroom door, letting hot steam billow out and humidify the bedroom for a moment, sighing in relief as the cool air conditioned room cooled his hot skin. Stiles was wearing one towel around his slim hips, his hair damp and limp against his forehead, face flushed from the heat.

"Woah." Stiles said, making eye contact with Derek and seeing his pupils were almost completely black with arousal. He smiled, the blush creeping down his neck, "You look... ready."

Derek squeezed his swollen length that lay on his hip through his pants, growling when Stiles dropped the towel and walked to him.

Derek grabbed him by the hips and hauled him into his lap, kissing him fiercely. Stiles immediately ground down onto Derek's length, and then forward to press his own dick into Derek's stomach, rolling and grinding.

Derek scooted both of them further down the bed so he could lay down all the way. Stiles kissed and nipped his way down Derek's body until he reached his night pants, where Derek was rock hard and had already made a wet mark the size of a quarter.

"We've only kissed Derek, are you sure you're up for this challenge?" Stiles giggled and smirked as he dug his hand under the waist band and pulled out Derek's cock, waggling it in a patronizing manner.

"Shut up and get the dildo, Stiles." Derek said, but not nearly as firmly as he meant it.

Stiles hopped up and got the dildo and lube, as well as the wolf muzzle fleshlight as Derek moved to the middle of the bed.

When Stiles came back, he pulled Derek's hips to straddle his and spread his legs. "I think you'll be surprised by this Derek." Stiles said as he squirted lube into his palm and slowly began stroking Derek's length and spread it around his balls.

"D-Doubt it." Derek said, toes curling when Stiles made a tight ring with his fingers, slowly stroking up and squeezing around the head and pulling so the tip purposefully had to pop out. Stiles didn't yet know about the plug, and the pressure inside Derek grew as his arousal swelled his prostate. Combined with the tension in the tip of his dick and he already felt like he was going to shoot soon.

When Stiles's left hand made it's way down Derek's cheeks to press on his hole, Stiles's gasped and stared at Derek before his eyes darkened and he grinned like the fucking cheshire cat.

Derek began to tremble under his gaze. "Someone is certainly ready aren't they? Is this a little surprise for me? You love the feeling of being filled don't you?" Stiles hooked his finger in the ring of the plug and slowly pulled, watching Derek's hole gape as it extended.

"If there was any indication that you like having your ass filled," The plug reached the widest part and Stiles let go so it harshly popped back in, jarring Derek's prostate and making him jump. "This would be it."

"Stiles, I can't for too much longer." Derek huffed, cheeks pink and jaw set.

Stiles slowly pulled the plug out all the way and discarded it. He grabbed the double ended dildo and spread lube across it, pressing it to Derek's hole, and slowly but firmly pressing.

Derek's entrance had apparently tightened again with the plug inside, and it was a little painful getting past it, but once the tip was inside, he felt like his insides melted and swallowed it down. He moaned as the smooth bumps created delicious friction and pinpoint pressure inside.

He moaned even louder as Stiles pushed the dildo all the way in until the knot touched his cheeks. His body was trembling and his entire anal cavity seemed to be clenching and pulsing around the toy.

"Derek you need to breath. This is a challenge after all." Stiles said as he spread lube along the other end. Derek twitched as Stiles's fingers stroked the dildo, feeling the motions deep inside.

Stiles was right. He needed to compose himself. He wasn't going to let Stiles win. He would make Stiles cry first. That was achievable. He'd done it many times before.

He watched hungrily as Stiles spread his own legs, showing off his hole, and spreading lube along it, immediately pushing two fingers in. Stiles was weird like that, Derek thought. Stiles liked the burn and sudden stretch. He only had his fingers inside long enough to spread the lube and then he was clutched the shaft of the dildo, bracing himself on his heels and one hand to push himself down onto the dildo.

Derek didnt often, actually never, get to watch from this angle as Stiles was breached. He watched as Stiles pushed hard, forcing the tip to pop viciously past Stiles's muscle. When it did, it jolted within Derek too and they both moaned.

Derek bit his lip at the sight of Stiles's hole clenching painfully down on the silicone. His own cock flexed, knowing what that felt like in his own experiences of Stiles adamantly demanding Derek to just get in him.

After a few minutes of catching their breath and laying there, Derek said, "Well now what?"

Stiles answered by pressing all the way down onto his end until the knot pressed against him. Derek's toes had curled as his own silicone knot had nearly pressed inside of him considering they were taking each other's weight internally.

Stiles, still braced on his heels and nearly squatting, began humping as if he was riding a cock, jostling and thrusting the dildo in Derek as well.

Derek spread his legs wider and took the fucking, enjoying the view he was getting of Stiles as well. It was a little tough since they were so close, and the positions didn't allow for much actual fucking, but Derek was still feeling an orgasm threatening him as the dildo was minutely thrusting within him.

He suddenly got an idea, and pushed Stiles down on his back and, sitting up, pulled himself off the toy. He hiked Stiles to the bed board, and propped him so his back was against the baord, hips up in the air.

Derek squatted over Stiles, and slowly pressed the dildo back in until the knot reached him. It was Stiles's turn to moan as the dildo was pushed deeper, and the knot harshly pushing against his hole.

Derek had a glint his eye, grabbing the base of the dildo against Stiles's ass and let gravity force the silicone knot into Derek. They both moaned and Derek's cock spat precum in a string on Stiles's own balls as Stiles's toes curled by his head.

Derek grabbed Stiles's ankles in his massive hands, and grinned predatorily down at Stiles.

"Derek what are-"

Derek leaned forward and began to viciously pump his hips as if he was riding a cock to town. The knot inside of him allowed him to pump the dildo in Stiles in a vicious fuck, who screamed and grabbed the comforter of the bed in a death grip as his hole immediately bore down. The friction of the bumps around the dildo burned and created obscene sounds within him.

Derek let his head fall back and his mind go blank as he fucked himself and his boyfriend to pieces. He couldn't get over the fact that he was simultaneously fucking himself and fucking Stiles. By the sound of Stiles's whines and cries, he was overwhelmed and the tears would come soon. This challenge was a little too easy.

When he looked back down, hands now braced on the headboard, he nearly came as Stiles was indeed crying. Red faced, and drooling, tears yet to be spilled, and mouth open as he was onslaught with pleasure pain. He was grappling shakily at Derek's ankles to ground himself and whimpering, "You're a bully, Derek. You're s-so mean. M-making me cry-ahh!"

"You gonna cum, Stiles? You gonna cum from me fucking you with my ass?" Derek began stroking himself, precum turning into a constant drip as his own knot began to swell at the base.

"I want the knot, I want the knot." Stiles chanted, spreading his cheeks with his hands.

Derek slowed his humping, stroking himself and pinching himself around the base to flood his knot faster, veins bulging and turning purple. "You want this knot, Stiles? You want this knot in your ass? It's so much better than this tiny rubber knot, yeah?"

Stiles actually nodded and wiggled his hips desperately for pleasure, making the dildo twist inside Derek who screwed visciously around it.

He suddenly sat his haunches down in a further squat, making Stiles scream again as the knot pressed and then popped inside. Now they were cheeks to cheeks. Derek was literally sitting on Stiles, balls resting against Stiles's and they both moaned. Stiles's face screwed up as he orgasm unexpectedly shot through him.

Derek felt Stiles's walls beating around the dildo, making it twitch and flex inside him. He fought his own orgasm by digging his nails into the headboard, his face shifting, fangs extending.

Stiles lay panting, covered in his own cum as Derek stifeled his orgasm.

Stiles regained his composure a bit and, in a fit of revenge, squirted a large amount of lube into the wolf mouth fleshlight and slammed it onto Derek's purple cock. Derek shouted, eyes shooting open to stare down in shock. The silicone mouth was stretched obscenely over his knot and he was shocked to find that it had ridges and bumps at the very end pressing against his tips.

His legs began to shake, and he was pretty sure he was already cumming as Stiles began pumping it in fast, hard strokes. The lube made loud slopping sounds every time it popped over his knot. Derek screamed and thrust his hips forward, head thrown back, arching as he came. Cum immediately poured out the sides of the mouth and pooled on Stiles's chest. They both moaned as Derek's movements jammed the dildo around.

"Fuck, fuck, Stiles, don't stop." Derek encompassed Stiles's hand in his own and began pumping even harder as a secong orgasm was following right after the first. Again he thrust his hips forward harshly, quaking head to toe, cum overflowing and coating his balls and thighs.

He suddenly stood up, popping both knots out of them, and stepping off completely. He pull the dildo out of Stiles and discarded it.  
He laid down and pulled Stiles to press stomach to stomach on their sides and shoved himself into Stiles. He was a much bigger stretch in width than the dildo, and Stiles cried out, clinging to Derek as he was pounded in a rush. His knot mostly deflated but his arousal not fading.

Derek was beyond reason and pounded Stiles with abandon, balls slapping against his backside and hugging him close for long minutes, both of them crying out and grunting.

When Derek felt his third orgasm build, he pulled back slightly to pump Stiles's dick, who was crying real tears again.

"Fuck, fuck, Derek, your knot is swelling. Your knot is swelling. I'm gonna cum oh god!" Derek slammed home, bursting inside Stiles and roaring. Stiles shooting long watery ropes as he came as well, scoring Derek in the chin.

It was a long while before they were able to retain thought and speak. When Stiles finally spoke his voice was hoarse. "So that's what knotting is like."

Derek put a hand to his eyes. "Shit. I didn't even ask for your permission. Stiles I'm so sorry."

"You're lucky that I love you and am heavy on the forgiving. Plus that was amazing. Next time though, I'd like it to be slow."

"You've never liked slow."

"Well I want to feel every inch of that all over again, but slower. Torture me with it." Stiles waggled his eyebrows.

"I don't know if I can control how fast I knot."

"Well we will just have to practice then, wont we?"

"Jesus."


End file.
